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Most Requested Journal Articles 1Q06-Chemistry and Related

Following is one of the journal articles most requested by researchers using CAS electronic products.

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57 chemical substances from this document. CAS subject entries for this document include: Solid phase synthesis; Glycopeptides; Oligosaccharides, preparation; and 1 additional concept.

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TITLE:	Prompt chemo-enzymatic synthesis of diverse complex-type oligosaccharides and its application to the solid-phase synthesis of a glycopeptide with Asn-linked sialyl-undeca- and asialo-nona-saccharides
AUTHOR(S):	Kajihara, Yasuhiro; Suzuki, Yasuhiro; Yamamoto, Naoki; Sasaki, Ken; Sakakibara, Tohru; Juneja, Lekh Raj
CORPORATE SOURCE:	Graduate School of Integrated Science, Yokohama City University, Yokohama, 236-0027, Japan
SOURCE:	Chemistry--A European Journal (2004), 10(4), 971-985 CODEN: CEUJED; ISSN: 0947-6539
PUBLISHER:	Wiley-VCH Verlag GmbH & Co. KGaA
LANGUAGE:	English

ABSTRACT:
We describe herein the prepn. of 24 pure asparagine-linked oligosaccharides (Asn-oligosaccharides) from asparagine-linked biantennary complex-type sialyl-undeca-saccharide [(NeuAc-.alpha.-2,6-Gal-.beta.-1,4-GlcNAc-.beta.-1,2-Man-.alpha.-1,6/1,3-)2- Man-.beta.-1,4-GlcNAc-.beta.-1,4-GlcNAc-.beta.-1-asparagine, 2] obtained from egg yolk. Our synthetic strategy aimed at adapting branch specific exo-glycosidases digestion (.beta.-D-galactosidase, N-acetyl-.beta.-D-glucosaminidase and .alpha.-D-mannosidase) of the individual asialo-branch after prepn. of mono-sialyl-oligosaccharides obtained from 2 by acid hydrolysis of NeuAc. In order to perform branch specific exo-glycosidase digestion, isolation of pure mono-sialyl-oligosaccharides obtained was essential. However, isolation of two kinds of mono-sialyl-oligosaccharides are difficult by HPLC due to their highly hydrophilic nature. Therefore, we examd. chem. protection with hydrophobic protecting (Fmoc and benzyl) groups. These chem. protection enabled us to sep. the mono-sialyl-oligosaccharides by use of a HPLC column (ODS) on synthetic scales. Using these pure mono-sialyl-oligosaccharides enable us to obtain 24 Asn-linked oligosaccharides (100 mg scale) within a few weeks by branch specific exo-glycosidase digestions (.alpha.-D-neuraminidase, .beta.-D-galactosidase, N-acetyl-.beta.-D-glucosaminidase and .alpha.-D-mannosidase). In addn., solid-phase synthesis of glycopeptide having Asn-linked sialyl-undeca- and asialo-nona-saccharides thus obtained, was also performed on an acid labile HMPA-PEGA resin.